Process of making phenylglycin.



UNITED STATES PATENT OFFICE.

ROBERT SCHMIDLI'N, OF HQCHST-ON-THE-MAIN, GERMANY,. ASSIGNOR TO FARBWERKE. VORM. MEISTER, LUCIUS & BRIINING, OF HGCHST-ON-THE- MAIN, GERMANY, A CORPORATION OF GERMANY.

PROCESS OF MAKING PHENYLGLYCIN.

Specification of Letters Patent,

Application filed May 23,1906. Serial No. 318,296.

- Patented Jan. 15, 1907.

That such a process would give rise to a satisfactory yield of phenylglycin .could not be anticipated in view of the absence of smoothness in the simple reaction between 1 anilin and chloracetic acid and of the activity with which the reduction of nitrobenzene by iron proceeds, this last f a'ct rendering it probable that the chloracetic acid could be reduced to acetic acid.

It is possible that the unex ectedly good result may be due to the insoliibility of the compound of iron with phenylglycin, which might protect the product from further reaction.

The invention consists in heating nitrobenzene or a homologue thereof with iron and chloracetic acid and may be illustrated as l follows:

Into a vessel provided with an agitator, reflux condenser, and thermometer are intro- 2 duced six hundred and twenty kilos of nitrobenzene, one thousand kilos of ground orotherwise subdivided cast-iron, and seventy kilos of anilin. The whole is heated to about 70 centigrade, whereupon a solution of four hundred and seventy kilos of monochloracetic acid in about one thousand liters of water is 90 centigrade.

. tion is introduced in such a manner that the gradually run in. The temperature of this chloracetic-acid solution, which is at first aboutcentigrade, is radually raised to The chloracetic-acid solumass may remain constantly boiling. The

heating is continued for another couple of hours at from 98 to 100 centigrade, and the mass is then neutralized with-a concentrated solution of sodium carbonate, for which purpose about six hundred kilos of calcined soda are needed. The mass is then distilled with steam. -About seventy kilos of anilin pass over and are used in a fresh operation. The mixture is then passed through a filter-press, and the residue is thoroughly washed with water. From the combined filtrate and washings, reduced to about three thousand liters, the phenylglycin is separated by adding the requisite quantity of a mineral acid.

The directions given above are solely for the purpose of illustrating the process. The proportions and other details may be varied.

If in the foregoing example for the nitrobenzene be substituted an equivalent quantity of orthometa or para-nitrotoluene, the

known tolylglycins are obtained.

Having now described my invention, what I claim is The herein-described process for making aromatic henylglycins, which consists in causing ch oracetic acid to act in the heat on aromatic nitrohydrocarbons in presence of iron, transforming the iron-glycinate thus obtained into alkali glycinate by means of alkalies, distilling off the excess of aromatic amin with steam and precipitating the glycin with dilute acids from the residue filtered from the ROBERT SOHMIDLIN.

Witnesses: 1

JEAN GRUND, CARL GRUND 

